Picolinic acid → Methyl 2-fluoro-4-[(pyridine-2-carbonyl)amino]benzoate

HRID 2080664Notes

Reaction equation

HRID 2080664 reaction equation
Cl.CN(C)CCCN=C=NCC.[NH2:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[C:16]([F:24])[CH:15]=1.[N:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31](O)=[O:32]>N1C=CC=CC=1>[F:24][C:16]1[CH:15]=[C:14]([NH:13][C:31]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][N:25]=2)=[O:32])[CH:23]=[CH:22][C:17]=1[C:18]([O:20][CH3:21])=[O:19]

Participants

5

Reactant 3

HCID 1018Picolinic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21957875Methyl 4-amino-2-fluorobenzoate

Product 1

HCID 57433539Methyl 2-fluoro-4-[(pyridine-2-carbonyl)amino]benzoateYield 92.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride was added to a pyridine (500 ml) solution of 18.9 g of methyl 4-amino-2-fluorobenzoate and 16.5 g of picolinic acid, and stirred at room temperature for 2 hours. The solvent was evaporated away under reduced pressure, 600 ml of ethyl acetate was added to the residue, the organic layer was washed with aqueous 0.25 N hydrochloric acid solution, aqueous 0.25 N sodium hydroxide solution and saturated saline water, dried, concentrated under reduced pressure, solidified from a mixed solvent of hexane/ethyl acetate, and the solid was taken out through filtration. This was dried under reduced pressure to obtain 28.3 g of the entitled compound as a white solid.

Workup

  1. customThe solvent was evaporated away under reduced pressure, 600 ml of ethyl acetate
  2. additionwas added to the residue
  3. washthe organic layer was washed with aqueous 0.25 N hydrochloric acid solution, aqueous 0.25 N sodium hydroxide solution and saturated saline water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. filtrationthe solid was taken out through filtration
  7. customThis was dried under reduced pressure

Sources & evidence

ORD record
ord-135766c053134bdfabd742c558af2346
Source dataset
uspto-grants-2011_04
Patent number
US07932394B2

Reaction notes

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